# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_2 _database_code_depnum_ccdc_archive 'CCDC 803644' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 Ni O2 S4' _chemical_formula_weight 381.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.1029(10) _cell_length_b 21.056(3) _cell_length_c 6.3665(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.526(16) _cell_angle_gamma 90.00 _cell_volume 804.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3598 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 1.719 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.902 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 3598 _diffrn_reflns_av_R_equivalents 0.0636 _diffrn_reflns_av_sigmaI/netI 0.0838 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1771 _reflns_number_gt 1171 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.3874P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1771 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1005 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1660 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.0000 0.0000 0.0000 0.0405(3) Uani 1 2 d S . . S11 S -0.2405(2) 0.00883(6) 0.2203(2) 0.0509(4) Uani 1 1 d . . . C12 C -0.0929(8) 0.0759(2) 0.3030(8) 0.0407(11) Uani 1 1 d . . . S13 S 0.1182(2) 0.08867(6) 0.1695(2) 0.0542(4) Uani 1 1 d . . . O14 O -0.1325(6) 0.11503(16) 0.4480(6) 0.0507(9) Uani 1 1 d . B . C15 C -0.3108(9) 0.1016(2) 0.5708(8) 0.0489(13) Uani 1 1 d . . . H15A H -0.4394 0.0834 0.4780 0.059 Uiso 1 1 calc R A 1 H15B H -0.2585 0.0715 0.6844 0.059 Uiso 1 1 calc R A 1 C6A C -0.3707(14) 0.1615(3) 0.6601(13) 0.096(3) Uani 0.447(12) 1 d P B 1 H6A H -0.4575 0.1816 0.5326 0.115 Uiso 0.447(12) 1 calc PR B 1 C7A C -0.268(2) 0.2098(6) 0.753(2) 0.063(5) Uiso 0.447(12) 1 d P B 1 H7A1 H -0.2647 0.2458 0.6589 0.075 Uiso 0.447(12) 1 calc PR B 1 H7A2 H -0.1187 0.2000 0.8290 0.075 Uiso 0.447(12) 1 calc PR B 1 C8A C -0.434(3) 0.2167(8) 0.898(3) 0.087(7) Uani 0.447(12) 1 d P B 1 H8A1 H -0.3703 0.2131 1.0483 0.104 Uiso 0.447(12) 1 calc PR B 1 H8A2 H -0.5258 0.2546 0.8703 0.104 Uiso 0.447(12) 1 calc PR B 1 C9A C -0.5455(12) 0.1591(3) 0.8065(11) 0.078(2) Uani 0.447(12) 1 d P B 1 H9A1 H -0.6981 0.1651 0.7337 0.094 Uiso 0.447(12) 1 calc PR B 1 H9A2 H -0.5314 0.1231 0.9030 0.094 Uiso 0.447(12) 1 calc PR B 1 C6B C -0.3707(14) 0.1615(3) 0.6601(13) 0.096(3) Uani 0.553(12) 1 d P B 2 H6B H -0.2338 0.1739 0.7574 0.115 Uiso 0.553(12) 1 calc PR B 2 C7B C -0.448(2) 0.2172(5) 0.569(2) 0.077(4) Uani 0.553(12) 1 d P B 2 H7B1 H -0.5191 0.2131 0.4203 0.092 Uiso 0.553(12) 1 calc PR B 2 H7B2 H -0.3377 0.2508 0.5870 0.092 Uiso 0.553(12) 1 calc PR B 2 C8B C -0.611(3) 0.2221(7) 0.720(3) 0.099(6) Uani 0.553(12) 1 d P B 2 H8B1 H -0.5760 0.2560 0.8236 0.119 Uiso 0.553(12) 1 calc PR B 2 H8B2 H -0.7649 0.2245 0.6478 0.119 Uiso 0.553(12) 1 calc PR B 2 C9B C -0.5455(12) 0.1591(3) 0.8065(11) 0.078(2) Uani 0.553(12) 1 d P B 2 H9B1 H -0.6585 0.1266 0.7691 0.094 Uiso 0.553(12) 1 calc PR B 2 H9B2 H -0.4834 0.1586 0.9580 0.094 Uiso 0.553(12) 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0396(6) 0.0401(6) 0.0448(6) -0.0068(4) 0.0158(4) -0.0032(4) S11 0.0512(8) 0.0472(8) 0.0612(9) -0.0168(6) 0.0284(7) -0.0136(6) C12 0.044(3) 0.029(2) 0.052(3) -0.001(2) 0.016(2) 0.000(2) S13 0.0532(9) 0.0515(8) 0.0655(10) -0.0186(7) 0.0307(7) -0.0164(6) O14 0.052(2) 0.0425(19) 0.065(2) -0.0132(17) 0.0295(18) -0.0078(17) C15 0.054(3) 0.044(3) 0.055(3) -0.002(2) 0.027(3) 0.000(3) C6A 0.131(7) 0.043(3) 0.145(7) -0.018(4) 0.109(6) -0.014(4) C8A 0.097(14) 0.096(13) 0.083(13) -0.039(10) 0.059(11) -0.031(10) C9A 0.093(5) 0.062(4) 0.099(5) -0.017(4) 0.067(4) -0.014(4) C6B 0.131(7) 0.043(3) 0.145(7) -0.018(4) 0.109(6) -0.014(4) C7B 0.091(10) 0.050(7) 0.105(10) 0.017(6) 0.059(8) 0.019(6) C8B 0.080(10) 0.116(13) 0.116(13) 0.007(10) 0.056(10) 0.016(9) C9B 0.093(5) 0.062(4) 0.099(5) -0.017(4) 0.067(4) -0.014(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 S13 2.2105(13) 3 ? Ni1 S13 2.2105(13) . ? Ni1 S11 2.2155(14) 3 ? Ni1 S11 2.2155(14) . ? S11 C12 1.705(5) . ? C12 O14 1.294(5) . ? C12 S13 1.689(5) . ? O14 C15 1.479(5) . ? C15 C6B 1.458(7) . ? C15 C6A 1.458(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C6A C7A 1.283(15) . ? C6A C9A 1.540(7) . ? C6A H6A 0.9800 . ? C7A C8A 1.498(18) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8A C9A 1.458(15) . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C9A H9A1 0.9700 . ? C9A H9A2 0.9700 . ? C6B C7B 1.355(13) . ? C6B C9B 1.540(7) . ? C6B H6B 0.9800 . ? C7B C8B 1.503(16) . ? C7B H7B1 0.9700 . ? C7B H7B2 0.9700 . ? C8B C9B 1.464(15) . ? C8B H8B1 0.9700 . ? C8B H8B2 0.9700 . ? C9B H9B1 0.9700 . ? C9B H9B2 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S13 Ni1 S13 180.0 3 . ? S13 Ni1 S11 79.33(5) 3 3 ? S13 Ni1 S11 100.67(5) . 3 ? S13 Ni1 S11 100.67(5) 3 . ? S13 Ni1 S11 79.33(5) . . ? S11 Ni1 S11 180.0 3 . ? C12 S11 Ni1 83.74(17) . . ? O14 C12 S13 121.1(3) . . ? O14 C12 S11 126.2(4) . . ? S13 C12 S11 112.7(3) . . ? C12 S13 Ni1 84.26(16) . . ? C12 O14 C15 120.4(4) . . ? C6B C15 C6A 0.0(6) . . ? C6B C15 O14 107.5(4) . . ? C6A C15 O14 107.5(4) . . ? C6B C15 H15A 110.2 . . ? C6A C15 H15A 110.2 . . ? O14 C15 H15A 110.2 . . ? C6B C15 H15B 110.2 . . ? C6A C15 H15B 110.2 . . ? O14 C15 H15B 110.2 . . ? H15A C15 H15B 108.5 . . ? C7A C6A C15 136.9(10) . . ? C7A C6A C9A 94.7(8) . . ? C15 C6A C9A 117.3(5) . . ? C7A C6A C8A 48.4(7) . . ? C15 C6A C8A 153.5(8) . . ? C9A C6A C8A 46.4(5) . . ? C7A C6A H6A 100.7 . . ? C15 C6A H6A 100.7 . . ? C9A C6A H6A 100.7 . . ? C8A C6A H6A 103.0 . . ? C6A C7A C8A 91.7(10) . . ? C6A C7A H7A1 113.3 . . ? C8A C7A H7A1 113.3 . . ? C6A C7A H7A2 113.3 . . ? C8A C7A H7A2 113.3 . . ? H7A1 C7A H7A2 110.7 . . ? C9A C8A C7A 89.6(9) . . ? C9A C8A H8A1 113.7 . . ? C7A C8A H8A1 113.7 . . ? C6A C8A H8A1 127.0 . . ? C9A C8A H8A2 113.7 . . ? C7A C8A H8A2 113.7 . . ? C6A C8A H8A2 121.7 . . ? H8A1 C8A H8A2 111.0 . . ? C8A C9A C6A 83.7(6) . . ? C8A C9A H9A1 114.7 . . ? C6A C9A H9A1 114.7 . . ? C8A C9A H9A2 114.7 . . ? C6A C9A H9A2 114.7 . . ? H9A1 C9A H9A2 111.8 . . ? C7B C6B C15 132.5(9) . . ? C7B C6B C9B 93.5(6) . . ? C15 C6B C9B 117.3(5) . . ? C7B C6B H6B 103.4 . . ? C15 C6B H6B 103.4 . . ? C9B C6B H6B 103.4 . . ? C8B C6B H6B 106.0 . . ? C6B C7B C8B 90.3(9) . . ? C6B C7B H7B1 113.6 . . ? C8B C7B H7B1 113.6 . . ? C6B C7B H7B2 113.6 . . ? C8B C7B H7B2 113.6 . . ? H7B1 C7B H7B2 110.9 . . ? C9B C8B C7B 90.8(8) . . ? C9B C8B H8B1 113.5 . . ? C7B C8B H8B1 113.5 . . ? C6B C8B H8B1 121.0 . . ? C9B C8B H8B2 113.5 . . ? C7B C8B H8B2 113.5 . . ? C6B C8B H8B2 128.0 . . ? H8B1 C8B H8B2 110.8 . . ? C8B C9B C6B 85.0(6) . . ? C8B C9B H9B1 114.5 . . ? C6B C9B H9B1 114.5 . . ? C8B C9B H9B2 114.5 . . ? C6B C9B H9B2 114.5 . . ? H9B1 C9B H9B2 111.6 . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.579 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.103 data_5 _database_code_depnum_ccdc_archive 'CCDC 834667' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 N4 Ni O2 S4' _chemical_formula_weight 585.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1216(11) _cell_length_b 10.3788(16) _cell_length_c 10.7918(9) _cell_angle_alpha 78.834(11) _cell_angle_beta 76.312(12) _cell_angle_gamma 83.671(13) _cell_volume 652.08(16) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4843 _cell_measurement_theta_min 3.43 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 302 _exptl_absorpt_coefficient_mu 1.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.83180 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 4830 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2842 _reflns_number_gt 1887 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.0955P)^2^+0.0980P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2842 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0897 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1758 _refine_ls_wR_factor_gt 0.1549 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.0000 0.0000 0.0000 0.0530(3) Uani 1 2 d S . . S11 S -0.21132(19) 0.04360(10) -0.14394(10) 0.0603(3) Uani 1 1 d . . . C12 C -0.2857(6) -0.1159(4) -0.0921(4) 0.0532(9) Uani 1 1 d . . . S13 S -0.14333(19) -0.19138(11) 0.02560(11) 0.0615(3) Uani 1 1 d . . . N14 N -0.4310(6) -0.1707(3) -0.1334(3) 0.0568(8) Uani 1 1 d . . . C21 C -0.5467(7) -0.0989(4) -0.2333(4) 0.0653(11) Uani 1 1 d . . . H21A H -0.5260 -0.0057 -0.2442 0.078 Uiso 1 1 calc R . . H21B H -0.7069 -0.1106 -0.2041 0.078 Uiso 1 1 calc R . . C22 C -0.4639(8) -0.1429(4) -0.3621(4) 0.0632(11) Uani 1 1 d . . . C23 C -0.2444(9) -0.1316(5) -0.4234(5) 0.0758(13) Uani 1 1 d . . . H23 H -0.1445 -0.0972 -0.3875 0.091 Uiso 1 1 calc R . . N24 N -0.1777(15) -0.1724(8) -0.5384(8) 0.153(3) Uani 1 1 d . . . C25 C -0.3416(19) -0.2123(8) -0.5807(8) 0.134(4) Uani 1 1 d . . . H25 H -0.2958 -0.2330 -0.6634 0.160 Uiso 1 1 calc R . . C26 C -0.553(2) -0.2279(8) -0.5287(9) 0.149(3) Uani 1 1 d . . . H26 H -0.6555 -0.2610 -0.5641 0.179 Uiso 1 1 calc R . . C27 C -0.5934(13) -0.1899(6) -0.4221(6) 0.109(2) Uani 1 1 d . . . H27 H -0.7423 -0.1959 -0.3765 0.131 Uiso 1 1 calc R . . C31 C -0.4893(8) -0.3063(5) -0.0782(5) 0.0695(12) Uani 1 1 d . A . H31A H -0.6514 -0.3100 -0.0625 0.083 Uiso 1 1 calc R . . H31B H -0.4464 -0.3312 0.0046 0.083 Uiso 1 1 calc R . . C32 C -0.3787(9) -0.4026(5) -0.1627(5) 0.0756(13) Uani 1 1 d . . . C33 C -0.1538(10) -0.4296(6) -0.1901(7) 0.140(3) Uani 1 1 d . . . H33 H -0.0481 -0.3962 -0.1576 0.168 Uiso 1 1 calc R . . C34 C -0.1108(17) -0.5189(8) -0.2781(9) 0.166(4) Uani 1 1 d . . . H34 H 0.0334 -0.5507 -0.3149 0.199 Uiso 1 1 calc R . . C35 C -0.305(3) -0.5544(7) -0.3042(9) 0.198(6) Uani 1 1 d . . . H35 H -0.3240 -0.6136 -0.3548 0.238 Uiso 1 1 calc R . . O36 O -0.4751(13) -0.4688(6) -0.2263(5) 0.137(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0539(5) 0.0606(5) 0.0420(4) -0.0144(3) -0.0037(3) 0.0017(3) S11 0.0663(7) 0.0614(6) 0.0507(6) -0.0092(5) -0.0113(5) 0.0014(5) C12 0.050(2) 0.065(2) 0.039(2) -0.0160(17) 0.0008(17) 0.0088(18) S13 0.0672(7) 0.0636(6) 0.0523(7) -0.0069(5) -0.0144(5) -0.0016(5) N14 0.0557(19) 0.067(2) 0.046(2) -0.0177(15) -0.0056(15) 0.0032(16) C21 0.055(2) 0.082(3) 0.061(3) -0.029(2) -0.014(2) 0.015(2) C22 0.071(3) 0.068(3) 0.049(2) -0.0145(19) -0.013(2) 0.011(2) C23 0.078(3) 0.089(3) 0.049(3) -0.025(2) 0.014(2) 0.008(2) N24 0.179(7) 0.141(6) 0.128(6) -0.009(4) -0.034(5) 0.010(5) C25 0.175(9) 0.114(6) 0.077(5) -0.006(4) 0.000(6) 0.058(6) C26 0.227(11) 0.130(6) 0.124(7) -0.051(5) -0.097(8) 0.027(7) C27 0.158(6) 0.107(4) 0.087(4) -0.035(3) -0.068(4) 0.009(4) C31 0.060(3) 0.085(3) 0.064(3) -0.017(2) -0.008(2) -0.014(2) C32 0.084(4) 0.066(3) 0.077(3) -0.012(2) -0.016(3) -0.010(2) C33 0.111(5) 0.134(5) 0.195(7) -0.088(5) -0.033(4) 0.016(3) C34 0.182(9) 0.119(6) 0.193(9) -0.096(6) -0.004(7) 0.047(6) C35 0.43(2) 0.069(4) 0.120(7) -0.027(4) -0.086(10) -0.023(8) O36 0.217(8) 0.110(4) 0.108(5) -0.016(3) -0.081(5) -0.018(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 S11 2.2002(11) . ? Ni1 S11 2.2002(11) 2 ? Ni1 S13 2.2019(11) . ? Ni1 S13 2.2020(11) 2 ? S11 C12 1.717(4) . ? C12 N14 1.308(5) . ? C12 S13 1.724(4) . ? N14 C31 1.465(5) . ? N14 C21 1.467(5) . ? C21 C22 1.503(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C27 1.318(7) . ? C22 C23 1.357(6) . ? C23 N24 1.347(9) . ? C23 H23 0.9300 . ? N24 C25 1.329(11) . ? C25 C26 1.300(11) . ? C25 H25 0.9300 . ? C26 C27 1.250(9) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C31 C32 1.484(7) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 O36 1.325(7) . ? C32 C36 1.325(7) . ? C32 C33 1.347(7) . ? C32 O33 1.347(7) . ? C33 C34 1.414(9) . ? C33 H33 0.9300 . ? O33 C34 1.414(9) . ? C34 C35 1.387(14) . ? C34 H34 0.9300 . ? C35 O36 1.501(13) . ? C35 C36 1.501(13) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S11 Ni1 S11 180.0 . 2 ? S11 Ni1 S13 79.22(4) . . ? S11 Ni1 S13 100.78(4) 2 . ? S11 Ni1 S13 100.78(4) . 2 ? S11 Ni1 S13 79.22(4) 2 2 ? S13 Ni1 S13 180.00(2) . 2 ? C12 S11 Ni1 85.85(14) . . ? N14 C12 S11 125.4(3) . . ? N14 C12 S13 125.3(3) . . ? S11 C12 S13 109.3(2) . . ? C12 S13 Ni1 85.61(14) . . ? C12 N14 C31 120.8(4) . . ? C12 N14 C21 121.9(4) . . ? C31 N14 C21 117.3(4) . . ? N14 C21 C22 113.4(3) . . ? N14 C21 H21A 108.9 . . ? C22 C21 H21A 108.9 . . ? N14 C21 H21B 108.9 . . ? C22 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C27 C22 C23 117.0(5) . . ? C27 C22 C21 123.9(5) . . ? C23 C22 C21 119.1(4) . . ? N24 C23 C22 117.0(6) . . ? N24 C23 H23 121.5 . . ? C22 C23 H23 121.5 . . ? C25 N24 C23 114.7(8) . . ? C26 C25 N24 132.4(9) . . ? C26 C25 H25 113.8 . . ? N24 C25 H25 113.8 . . ? C27 C26 C25 106.7(9) . . ? C27 C26 H26 126.6 . . ? C25 C26 H26 126.6 . . ? C26 C27 C22 132.0(9) . . ? C26 C27 H27 114.0 . . ? C22 C27 H27 114.0 . . ? N14 C31 C32 113.3(4) . . ? N14 C31 H31A 108.9 . . ? C32 C31 H31A 108.9 . . ? N14 C31 H31B 108.9 . . ? C32 C31 H31B 108.9 . . ? H31A C31 H31B 107.7 . . ? O36 C32 C36 0.0(5) . . ? O36 C32 C33 110.0(6) . . ? C36 C32 C33 110.0(6) . . ? O36 C32 O33 110.0(6) . . ? C36 C32 O33 110.0(6) . . ? C33 C32 O33 0.0 . . ? O36 C32 C31 127.5(6) . . ? C36 C32 C31 127.5(6) . . ? C33 C32 C31 122.4(5) . . ? O33 C32 C31 122.4(5) . . ? C32 C33 C34 106.2(6) . . ? C32 C33 H33 126.9 . . ? C34 C33 H33 126.9 . . ? C32 O33 C34 106.2(6) . . ? C35 C34 C33 113.3(8) . . ? C35 C34 O33 113.3(8) . . ? C33 C34 O33 0.0(4) . . ? C35 C34 H34 123.4 . . ? C33 C34 H34 123.4 . . ? O33 C34 H34 123.4 . . ? C34 C35 O36 99.0(6) . . ? C34 C35 C36 99.0(6) . . ? O36 C35 C36 0.0(5) . . ? C34 C35 H35 130.5 . . ? O36 C35 H35 130.5 . . ? C36 C35 H35 130.5 . . ? C32 C36 C35 111.5(8) . . ? C32 C36 H36 124.2 . . ? C35 C36 H36 124.2 . . ? C32 O36 C35 111.5(8) . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.736 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.071 data_6 _database_code_depnum_ccdc_archive 'CCDC 859863' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H24 N2 Ni O2 S4' _chemical_formula_weight 583.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2494(4) _cell_length_b 6.9702(5) _cell_length_c 15.3641(13) _cell_angle_alpha 80.996(6) _cell_angle_beta 82.990(6) _cell_angle_gamma 89.460(5) _cell_volume 656.03(8) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4914 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 302 _exptl_absorpt_coefficient_mu 1.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.96102 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 4914 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2857 _reflns_number_gt 1993 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.0733P)^2^+0.3197P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2857 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1526 _refine_ls_wR_factor_gt 0.1374 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N14 N -0.0521(5) -0.2178(5) 0.1365(2) 0.0502(8) Uani 1 1 d . . . S11 S 0.28433(16) -0.25201(17) 0.01205(7) 0.0579(3) Uani 1 1 d . . . S13 S 0.25081(16) 0.06654(16) 0.10459(7) 0.0579(3) Uani 1 1 d . . . Ni1 Ni 0.5000 0.0000 0.0000 0.0489(3) Uani 1 2 d S . . C12 C 0.1289(6) -0.1463(6) 0.0923(2) 0.0489(9) Uani 1 1 d . . . C21 C -0.1849(6) -0.1087(6) 0.1973(3) 0.0534(10) Uani 1 1 d . . . H21A H -0.3352 -0.1233 0.1894 0.064 Uiso 1 1 calc R . . H21B H -0.1474 0.0281 0.1814 0.064 Uiso 1 1 calc R . . C22 C -0.1590(7) -0.1724(6) 0.2937(3) 0.0579(11) Uani 1 1 d . . . C23 C 0.0320(8) -0.1691(10) 0.3262(3) 0.0912(18) Uani 1 1 d . . . H23 H 0.1568 -0.1304 0.2882 0.109 Uiso 1 1 calc R . . C24 C 0.0410(13) -0.2223(15) 0.4140(5) 0.148(4) Uani 1 1 d . . . H24 H 0.1726 -0.2240 0.4366 0.178 Uiso 1 1 calc R . . C25 C -0.1291(16) -0.2695(15) 0.4650(6) 0.153(3) Uani 1 1 d . . . H25 H -0.1180 -0.3026 0.5253 0.184 Uiso 1 1 calc R . . C26 C -0.3142(13) -0.2755(11) 0.4404(5) 0.111(2) Uani 1 1 d . . . H26 H -0.4347 -0.3115 0.4814 0.133 Uiso 1 1 calc R . . C27 C -0.3320(7) -0.2284(6) 0.3536(3) 0.0629(12) Uani 1 1 d . . . H27 H -0.4667 -0.2344 0.3342 0.076 Uiso 1 1 calc R . . C31 C -0.1447(7) -0.3985(7) 0.1166(3) 0.0636(12) Uani 1 1 d . A . H31A H -0.0292 -0.4740 0.0911 0.076 Uiso 1 1 calc R . . H31B H -0.2429 -0.3645 0.0725 0.076 Uiso 1 1 calc R . . C32 C -0.2621(7) -0.5208(6) 0.1955(3) 0.0519(10) Uani 1 1 d . . . O33 O -0.1488(6) -0.6118(5) 0.2594(3) 0.0786(14) Uani 1 1 d . . . C34 C -0.2996(15) -0.7229(8) 0.3259(4) 0.120(3) Uani 1 1 d . . . H34 H -0.2670 -0.7976 0.3781 0.144 Uiso 1 1 calc R A 1 C35 C -0.5115(12) -0.6979(10) 0.2971(5) 0.119(3) Uani 1 1 d . A . H35 H -0.6415 -0.7529 0.3255 0.143 Uiso 1 1 calc R B 1 C36 C -0.4734(7) -0.5658(8) 0.2127(3) 0.086(2) Uani 1 1 d . . . H36 H -0.5784 -0.5203 0.1768 0.103 Uiso 1 1 calc PR A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N14 0.0514(18) 0.058(2) 0.0395(17) -0.0093(15) 0.0040(14) -0.0179(15) S11 0.0547(6) 0.0683(7) 0.0503(6) -0.0201(5) 0.0101(4) -0.0217(5) S13 0.0552(6) 0.0617(7) 0.0559(6) -0.0170(5) 0.0088(5) -0.0202(5) Ni1 0.0441(4) 0.0609(5) 0.0405(4) -0.0089(3) 0.0017(3) -0.0160(3) C12 0.051(2) 0.060(3) 0.0346(19) -0.0062(18) -0.0013(16) -0.0137(18) C21 0.045(2) 0.060(3) 0.052(2) -0.005(2) 0.0035(17) -0.0041(18) C22 0.062(2) 0.066(3) 0.045(2) -0.016(2) 0.0056(19) -0.004(2) C23 0.066(3) 0.156(6) 0.047(3) -0.008(3) -0.001(2) -0.006(3) C24 0.110(5) 0.267(12) 0.063(4) -0.014(6) -0.008(4) -0.005(6) C25 0.143(7) 0.202(10) 0.113(7) -0.034(7) 0.000(6) 0.017(7) C26 0.129(6) 0.123(6) 0.077(4) -0.014(4) 0.004(4) -0.008(5) C27 0.075(3) 0.067(3) 0.043(2) -0.009(2) 0.011(2) -0.011(2) C31 0.069(3) 0.073(3) 0.048(2) -0.017(2) 0.008(2) -0.032(2) C32 0.057(2) 0.052(2) 0.045(2) -0.0096(19) 0.0034(18) -0.0134(19) O33 0.093(3) 0.070(3) 0.075(3) -0.019(2) -0.007(2) 0.005(2) C34 0.232(9) 0.053(3) 0.069(4) -0.015(3) 0.018(5) -0.008(5) C35 0.125(5) 0.106(5) 0.119(6) -0.048(4) 0.064(5) -0.064(4) O36 0.071(3) 0.105(4) 0.080(4) -0.020(3) 0.011(2) -0.030(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N14 C12 1.306(4) . ? N14 C21 1.469(5) . ? N14 C31 1.480(5) . ? S11 C12 1.728(4) . ? S11 Ni1 2.1951(10) . ? S13 C12 1.721(4) . ? S13 Ni1 2.1980(10) . ? Ni1 S11 2.1951(10) 2_655 ? Ni1 S13 2.1980(10) 2_655 ? C21 C22 1.506(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C27 1.349(5) . ? C22 C23 1.351(6) . ? C23 C24 1.350(8) . ? C23 H23 0.9300 . ? C24 C25 1.255(10) . ? C24 H24 0.9300 . ? C25 C26 1.263(10) . ? C25 H25 0.9300 . ? C26 C27 1.341(8) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C31 C32 1.484(5) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 O36 1.345(6) . ? C32 C36 1.345(6) . ? C32 C33 1.355(6) . ? C32 O33 1.355(6) . ? C33 C34 1.436(7) . ? C33 H33 0.9300 . ? O33 C34 1.436(7) . ? C34 C35 1.447(10) . ? C34 H34 0.9300 . ? C35 O36 1.462(9) . ? C35 C36 1.462(9) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N14 C21 121.4(3) . . ? C12 N14 C31 120.3(3) . . ? C21 N14 C31 117.7(3) . . ? C12 S11 Ni1 85.59(13) . . ? C12 S13 Ni1 85.65(13) . . ? S11 Ni1 S11 180.0 . 2_655 ? S11 Ni1 S13 79.57(4) . . ? S11 Ni1 S13 100.43(4) 2_655 . ? S11 Ni1 S13 100.43(4) . 2_655 ? S11 Ni1 S13 79.57(4) 2_655 2_655 ? S13 Ni1 S13 180.0 . 2_655 ? N14 C12 S13 125.7(3) . . ? N14 C12 S11 125.1(3) . . ? S13 C12 S11 109.2(2) . . ? N14 C21 C22 113.9(3) . . ? N14 C21 H21A 108.8 . . ? C22 C21 H21A 108.8 . . ? N14 C21 H21B 108.8 . . ? C22 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C27 C22 C23 116.2(4) . . ? C27 C22 C21 120.6(4) . . ? C23 C22 C21 123.2(4) . . ? C24 C23 C22 119.7(5) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C25 C24 C23 119.7(8) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 124.7(10) . . ? C24 C25 H25 117.6 . . ? C26 C25 H25 117.6 . . ? C25 C26 C27 118.1(8) . . ? C25 C26 H26 120.9 . . ? C27 C26 H26 120.9 . . ? C26 C27 C22 121.5(5) . . ? C26 C27 H27 119.2 . . ? C22 C27 H27 119.2 . . ? N14 C31 C32 113.8(3) . . ? N14 C31 H31A 108.8 . . ? C32 C31 H31A 108.8 . . ? N14 C31 H31B 108.8 . . ? C32 C31 H31B 108.8 . . ? H31A C31 H31B 107.7 . . ? O36 C32 C36 0.0(7) . . ? O36 C32 C33 111.9(4) . . ? C36 C32 C33 111.9(4) . . ? O36 C32 O33 111.9(4) . . ? C36 C32 O33 111.9(4) . . ? C33 C32 O33 0.0(4) . . ? O36 C32 C31 129.0(5) . . ? C36 C32 C31 129.0(5) . . ? C33 C32 C31 119.0(4) . . ? O33 C32 C31 119.0(4) . . ? C32 C33 C34 107.4(5) . . ? C32 C33 H33 126.3 . . ? C34 C33 H33 126.3 . . ? C32 O33 C34 107.4(5) . . ? O33 C34 C33 0.0(4) . . ? O33 C34 C35 107.8(6) . . ? C33 C34 C35 107.8(6) . . ? O33 C34 H34 126.1 . . ? C33 C34 H34 126.1 . . ? C35 C34 H34 126.1 . . ? C34 C35 O36 103.8(5) . . ? C34 C35 C36 103.8(5) . . ? O36 C35 C36 0.0(3) . . ? C34 C35 H35 128.1 . . ? O36 C35 H35 128.1 . . ? C36 C35 H35 128.1 . . ? C32 C36 C35 109.0(5) . . ? C32 C36 H36 125.5 . . ? C35 C36 H36 125.5 . . ? C32 O36 C35 109.0(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 S11 Ni1 S11 -122(6) . . . 2_655 ? C12 S11 Ni1 S13 0.45(14) . . . . ? C12 S11 Ni1 S13 -179.55(14) . . . 2_655 ? C12 S13 Ni1 S11 -0.45(14) . . . . ? C12 S13 Ni1 S11 179.55(14) . . . 2_655 ? C12 S13 Ni1 S13 38(2) . . . 2_655 ? C21 N14 C12 S13 6.3(6) . . . . ? C31 N14 C12 S13 177.3(3) . . . . ? C21 N14 C12 S11 -173.8(3) . . . . ? C31 N14 C12 S11 -2.9(6) . . . . ? Ni1 S13 C12 N14 -179.6(4) . . . . ? Ni1 S13 C12 S11 0.60(19) . . . . ? Ni1 S11 C12 N14 179.6(4) . . . . ? Ni1 S11 C12 S13 -0.60(19) . . . . ? C12 N14 C21 C22 -100.5(4) . . . . ? C31 N14 C21 C22 88.3(4) . . . . ? N14 C21 C22 C27 -124.4(4) . . . . ? N14 C21 C22 C23 58.6(6) . . . . ? C27 C22 C23 C24 0.7(10) . . . . ? C21 C22 C23 C24 177.8(6) . . . . ? C22 C23 C24 C25 -1.8(14) . . . . ? C23 C24 C25 C26 1.5(18) . . . . ? C24 C25 C26 C27 0.1(17) . . . . ? C25 C26 C27 C22 -1.3(11) . . . . ? C23 C22 C27 C26 0.8(8) . . . . ? C21 C22 C27 C26 -176.3(5) . . . . ? C12 N14 C31 C32 146.8(4) . . . . ? C21 N14 C31 C32 -41.9(6) . . . . ? N14 C31 C32 O36 114.3(5) . . . . ? N14 C31 C32 C36 114.3(5) . . . . ? N14 C31 C32 C33 -69.3(5) . . . . ? N14 C31 C32 O33 -69.3(5) . . . . ? O36 C32 C33 C34 -1.6(5) . . . . ? C36 C32 C33 C34 -1.6(5) . . . . ? O33 C32 C33 C34 0(100) . . . . ? C31 C32 C33 C34 -178.5(4) . . . . ? O36 C32 O33 C34 -1.6(5) . . . . ? C36 C32 O33 C34 -1.6(5) . . . . ? C33 C32 O33 C34 0(100) . . . . ? C31 C32 O33 C34 -178.5(4) . . . . ? C32 O33 C34 C33 0(100) . . . . ? C32 O33 C34 C35 1.6(6) . . . . ? C32 C33 C34 O33 0(100) . . . . ? C32 C33 C34 C35 1.6(6) . . . . ? O33 C34 C35 O36 -1.0(6) . . . . ? C33 C34 C35 O36 -1.0(6) . . . . ? O33 C34 C35 C36 -1.0(6) . . . . ? C33 C34 C35 C36 -1.0(6) . . . . ? O36 C32 C36 C35 0(100) . . . . ? C33 C32 C36 C35 1.0(6) . . . . ? O33 C32 C36 C35 1.0(6) . . . . ? C31 C32 C36 C35 177.5(4) . . . . ? C34 C35 C36 C32 0.0(6) . . . . ? O36 C35 C36 C32 0(100) . . . . ? C36 C32 O36 C35 0(100) . . . . ? C33 C32 O36 C35 1.0(6) . . . . ? O33 C32 O36 C35 1.0(6) . . . . ? C31 C32 O36 C35 177.5(4) . . . . ? C34 C35 O36 C32 0.0(6) . . . . ? C36 C35 O36 C32 0(100) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.815 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.068 data_l _database_code_depnum_ccdc_archive 'CCDC 913784' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H22 Ni O2 S4' _chemical_formula_weight 601.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.2196(9) _cell_length_b 5.8144(3) _cell_length_c 13.3549(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.728(5) _cell_angle_gamma 90.00 _cell_volume 1321.63(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6335 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 27.50 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620 _exptl_absorpt_coefficient_mu 1.078 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 6335 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0857 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2906 _reflns_number_gt 1835 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.6643P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2906 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1090 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C12 C 0.4196(2) 0.1221(7) 0.3259(3) 0.0366(10) Uani 1 1 d . . . C15 C 0.3431(3) 0.0034(8) 0.1719(3) 0.0422(11) Uani 1 1 d . . . H15A H 0.3242 -0.1286 0.2055 0.051 Uiso 1 1 calc R . . H15B H 0.3861 -0.0462 0.1378 0.051 Uiso 1 1 calc R . . C21 C 0.2776(2) 0.1025(8) 0.0959(3) 0.0396(11) Uani 1 1 d . . . H21 H 0.2977 0.2229 0.0554 0.048 Uiso 1 1 calc R . . C22 C 0.2414(2) -0.0906(8) 0.0287(3) 0.0389(10) Uani 1 1 d . . . C23 C 0.2762(3) -0.2387(9) -0.0319(3) 0.0530(13) Uani 1 1 d . . . H23 H 0.3287 -0.2208 -0.0392 0.064 Uiso 1 1 calc R . . C24 C 0.2318(3) -0.4140(9) -0.0818(4) 0.0593(14) Uani 1 1 d . . . H24 H 0.2547 -0.5126 -0.1238 0.071 Uiso 1 1 calc R . . C25 C 0.1550(3) -0.4446(9) -0.0703(3) 0.0565(14) Uani 1 1 d . . . H25 H 0.1265 -0.5652 -0.1036 0.068 Uiso 1 1 calc R . . C26 C 0.1190(3) -0.2981(8) -0.0095(3) 0.0487(12) Uani 1 1 d . . . H26 H 0.0667 -0.3189 -0.0016 0.058 Uiso 1 1 calc R . . C27 C 0.1630(3) -0.1194(8) 0.0393(3) 0.0379(10) Uani 1 1 d . . . C28 C 0.1414(2) 0.0575(8) 0.1081(3) 0.0386(10) Uani 1 1 d . . . C29 C 0.0705(3) 0.1101(9) 0.1388(3) 0.0497(12) Uani 1 1 d . . . H29 H 0.0263 0.0212 0.1170 0.060 Uiso 1 1 calc R . . C30 C 0.0656(3) 0.2944(9) 0.2020(4) 0.0550(14) Uani 1 1 d . . . H30 H 0.0177 0.3320 0.2217 0.066 Uiso 1 1 calc R . . C31 C 0.1312(3) 0.4234(9) 0.2361(3) 0.0555(13) Uani 1 1 d . . . H31 H 0.1271 0.5461 0.2797 0.067 Uiso 1 1 calc R . . C32 C 0.2031(3) 0.3741(8) 0.2069(3) 0.0469(12) Uani 1 1 d . . . H32 H 0.2471 0.4628 0.2302 0.056 Uiso 1 1 calc R . . C33 C 0.2085(2) 0.1902(7) 0.1422(3) 0.0379(10) Uani 1 1 d . . . O14 O 0.37016(17) 0.1825(5) 0.2463(2) 0.0435(8) Uani 1 1 d . . . S11 S 0.44287(7) 0.3047(2) 0.42473(9) 0.0490(4) Uani 1 1 d . . . S13 S 0.46077(7) -0.1387(2) 0.34694(9) 0.0475(3) Uani 1 1 d . . . Ni1 Ni 0.5000 0.0000 0.5000 0.0360(2) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C12 0.035(2) 0.032(2) 0.042(2) 0.006(2) 0.0053(19) -0.005(2) C15 0.040(2) 0.043(3) 0.043(2) 0.003(2) 0.002(2) 0.003(2) C21 0.037(2) 0.045(3) 0.036(2) 0.000(2) 0.0034(19) -0.004(2) C22 0.038(2) 0.046(3) 0.033(2) 0.002(2) 0.0031(18) 0.006(2) C23 0.051(3) 0.064(3) 0.044(3) -0.008(3) 0.007(2) 0.009(3) C24 0.078(4) 0.057(3) 0.042(3) -0.010(3) 0.007(3) 0.019(3) C25 0.071(4) 0.052(3) 0.039(3) -0.002(3) -0.013(2) -0.006(3) C26 0.046(3) 0.055(3) 0.042(3) 0.006(3) -0.004(2) 0.003(3) C27 0.047(3) 0.039(3) 0.026(2) 0.002(2) 0.0002(18) 0.008(2) C28 0.037(2) 0.044(3) 0.032(2) 0.010(2) -0.0035(18) 0.004(2) C29 0.039(3) 0.063(3) 0.046(3) 0.005(3) 0.004(2) 0.001(3) C30 0.050(3) 0.068(4) 0.048(3) 0.000(3) 0.012(2) 0.015(3) C31 0.071(4) 0.054(3) 0.042(3) -0.006(3) 0.010(3) 0.014(3) C32 0.051(3) 0.044(3) 0.042(3) 0.005(2) -0.003(2) -0.001(2) C33 0.041(2) 0.039(3) 0.032(2) 0.008(2) -0.0011(18) 0.005(2) O14 0.0426(17) 0.0365(18) 0.0465(17) 0.0039(16) -0.0084(14) -0.0009(15) S11 0.0579(8) 0.0344(7) 0.0491(7) -0.0012(6) -0.0098(6) 0.0066(6) S13 0.0559(7) 0.0423(7) 0.0413(6) -0.0031(6) -0.0022(5) 0.0145(6) Ni1 0.0368(4) 0.0338(5) 0.0362(4) 0.0020(4) 0.0012(3) 0.0043(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C12 O14 1.306(5) . ? C12 S13 1.679(5) . ? C12 S11 1.694(4) . ? C15 O14 1.465(5) . ? C15 C21 1.513(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C21 C33 1.510(6) . ? C21 C22 1.511(6) . ? C21 H21 0.9800 . ? C22 C23 1.380(6) . ? C22 C27 1.389(6) . ? C23 C24 1.382(7) . ? C23 H23 0.9300 . ? C24 C25 1.367(7) . ? C24 H24 0.9300 . ? C25 C26 1.386(7) . ? C25 H25 0.9300 . ? C26 C27 1.388(6) . ? C26 H26 0.9300 . ? C27 C28 1.464(6) . ? C28 C29 1.380(6) . ? C28 C33 1.406(6) . ? C29 C30 1.374(6) . ? C29 H29 0.9300 . ? C30 C31 1.374(7) . ? C30 H30 0.9300 . ? C31 C32 1.385(7) . ? C31 H31 0.9300 . ? C32 C33 1.386(6) . ? C32 H32 0.9300 . ? S11 Ni1 2.1946(12) . ? S13 Ni1 2.2059(11) . ? Ni1 S11 2.1946(12) 3_656 ? Ni1 S13 2.2059(12) 3_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O14 C12 S13 125.8(3) . . ? O14 C12 S11 120.9(3) . . ? S13 C12 S11 113.1(2) . . ? O14 C15 C21 108.2(3) . . ? O14 C15 H15A 110.1 . . ? C21 C15 H15A 110.1 . . ? O14 C15 H15B 110.1 . . ? C21 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? C33 C21 C22 102.4(3) . . ? C33 C21 C15 114.1(3) . . ? C22 C21 C15 108.3(4) . . ? C33 C21 H21 110.6 . . ? C22 C21 H21 110.6 . . ? C15 C21 H21 110.6 . . ? C23 C22 C27 120.0(4) . . ? C23 C22 C21 129.5(4) . . ? C27 C22 C21 110.4(4) . . ? C22 C23 C24 119.1(5) . . ? C22 C23 H23 120.5 . . ? C24 C23 H23 120.5 . . ? C25 C24 C23 121.0(5) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C24 C25 C26 120.8(5) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C25 C26 C27 118.3(5) . . ? C25 C26 H26 120.8 . . ? C27 C26 H26 120.8 . . ? C26 C27 C22 120.8(4) . . ? C26 C27 C28 130.4(4) . . ? C22 C27 C28 108.8(4) . . ? C29 C28 C33 120.1(4) . . ? C29 C28 C27 131.5(4) . . ? C33 C28 C27 108.4(4) . . ? C30 C29 C28 119.7(5) . . ? C30 C29 H29 120.2 . . ? C28 C29 H29 120.2 . . ? C29 C30 C31 120.4(5) . . ? C29 C30 H30 119.8 . . ? C31 C30 H30 119.8 . . ? C30 C31 C32 121.2(5) . . ? C30 C31 H31 119.4 . . ? C32 C31 H31 119.4 . . ? C31 C32 C33 118.9(4) . . ? C31 C32 H32 120.6 . . ? C33 C32 H32 120.6 . . ? C32 C33 C28 119.7(4) . . ? C32 C33 C21 130.3(4) . . ? C28 C33 C21 109.9(4) . . ? C12 O14 C15 117.5(3) . . ? C12 S11 Ni1 83.54(15) . . ? C12 S13 Ni1 83.50(15) . . ? S11 Ni1 S11 180.0 . 3_656 ? S11 Ni1 S13 79.50(4) . . ? S11 Ni1 S13 100.50(4) 3_656 . ? S11 Ni1 S13 100.50(4) . 3_656 ? S11 Ni1 S13 79.50(4) 3_656 3_656 ? S13 Ni1 S13 180.0 . 3_656 ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.384 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.082 data_3 _database_code_depnum_ccdc_archive 'CCDC 913785' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H32 N2 Ni O2 S4' _chemical_formula_weight 591.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4140(6) _cell_length_b 7.9477(8) _cell_length_c 14.5825(13) _cell_angle_alpha 98.677(8) _cell_angle_beta 97.771(8) _cell_angle_gamma 106.057(9) _cell_volume 693.83(11) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5170 _cell_measurement_theta_min 3.32 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 310 _exptl_absorpt_coefficient_mu 1.026 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.940 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 5170 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.1568 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3039 _reflns_number_gt 1423 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.0274P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3039 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1713 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1239 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 0.903 _refine_ls_restrained_S_all 0.903 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.0000 1.0000 1.0000 0.0411(3) Uani 1 2 d S . . S11 S 0.2198(2) 0.84009(18) 0.96331(9) 0.0485(4) Uani 1 1 d . . . C12 C 0.0057(8) 0.7292(6) 0.8732(3) 0.0408(12) Uani 1 1 d . . . S13 S -0.2083(2) 0.8125(2) 0.87283(9) 0.0570(4) Uani 1 1 d . . . O14 O -0.0034(5) 0.5922(4) 0.8091(2) 0.0480(9) Uani 1 1 d . . . C15 C 0.1850(8) 0.5181(6) 0.8115(3) 0.0415(13) Uani 1 1 d . . . H15 H 0.3242 0.6155 0.8313 0.050 Uiso 1 1 calc R . . C16 C 0.1692(9) 0.4240(7) 0.7115(3) 0.0516(15) Uani 1 1 d . . . H16A H 0.0236 0.3385 0.6889 0.062 Uiso 1 1 calc R . . H16B H 0.1913 0.5103 0.6705 0.062 Uiso 1 1 calc R . . C17 C 0.3432(8) 0.3283(7) 0.7089(3) 0.0510(15) Uani 1 1 d . . . H17A H 0.3314 0.2661 0.6450 0.061 Uiso 1 1 calc R . . H17B H 0.4890 0.4147 0.7283 0.061 Uiso 1 1 calc R . . N18 N 0.3143(7) 0.2003(5) 0.7720(2) 0.0436(11) Uani 1 1 d . . . C19 C 0.3470(8) 0.2974(7) 0.8688(3) 0.0510(14) Uani 1 1 d . . . H19A H 0.4921 0.3852 0.8854 0.061 Uiso 1 1 calc R . . H19B H 0.3391 0.2149 0.9118 0.061 Uiso 1 1 calc R . . C20 C 0.1711(8) 0.3904(7) 0.8783(3) 0.0470(14) Uani 1 1 d . . . H20A H 0.0259 0.3027 0.8636 0.056 Uiso 1 1 calc R . . H20B H 0.1937 0.4549 0.9426 0.056 Uiso 1 1 calc R . . C21 C 0.4683(9) 0.0959(7) 0.7650(3) 0.0582(15) Uani 1 1 d . . . H21A H 0.4665 0.0318 0.8166 0.070 Uiso 1 1 calc R . . H21B H 0.6163 0.1769 0.7722 0.070 Uiso 1 1 calc R . . C22 C 0.4176(9) -0.0362(7) 0.6733(3) 0.0446(13) Uani 1 1 d . . . C23 C 0.5838(9) -0.0856(8) 0.6378(3) 0.0648(17) Uani 1 1 d . . . H23 H 0.7295 -0.0333 0.6689 0.078 Uiso 1 1 calc R . . C24 C 0.5354(11) -0.2137(9) 0.5554(4) 0.079(2) Uani 1 1 d . . . H24 H 0.6492 -0.2481 0.5327 0.094 Uiso 1 1 calc R . . C25 C 0.3257(11) -0.2894(8) 0.5076(4) 0.0724(19) Uani 1 1 d . . . H25 H 0.2962 -0.3720 0.4515 0.087 Uiso 1 1 calc R . . C26 C 0.1585(10) -0.2438(8) 0.5423(4) 0.0660(17) Uani 1 1 d . . . H26 H 0.0135 -0.2963 0.5105 0.079 Uiso 1 1 calc R . . C27 C 0.2053(9) -0.1184(7) 0.6254(4) 0.0624(16) Uani 1 1 d . . . H27 H 0.0897 -0.0894 0.6493 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0361(6) 0.0357(6) 0.0496(6) -0.0016(5) 0.0039(5) 0.0150(5) S11 0.0401(8) 0.0472(9) 0.0555(8) -0.0048(7) -0.0002(7) 0.0209(7) C12 0.038(3) 0.041(3) 0.044(3) 0.006(3) 0.007(3) 0.014(3) S13 0.0435(9) 0.0573(10) 0.0657(9) -0.0098(8) -0.0064(8) 0.0274(8) O14 0.042(2) 0.049(2) 0.050(2) -0.0076(18) -0.0018(18) 0.0229(19) C15 0.039(3) 0.040(3) 0.049(3) 0.003(3) 0.010(3) 0.020(3) C16 0.070(4) 0.052(4) 0.041(3) 0.008(3) 0.010(3) 0.033(3) C17 0.063(4) 0.054(4) 0.043(3) 0.009(3) 0.020(3) 0.024(3) N18 0.055(3) 0.043(3) 0.040(2) 0.006(2) 0.009(2) 0.028(2) C19 0.052(4) 0.059(4) 0.045(3) 0.013(3) 0.006(3) 0.023(3) C20 0.055(4) 0.053(4) 0.036(3) 0.002(3) 0.012(3) 0.022(3) C21 0.068(4) 0.052(4) 0.057(3) 0.001(3) 0.003(3) 0.032(3) C22 0.050(4) 0.043(3) 0.048(3) 0.012(3) 0.010(3) 0.023(3) C23 0.055(4) 0.086(5) 0.058(4) 0.000(3) 0.011(3) 0.035(4) C24 0.069(5) 0.119(6) 0.063(4) 0.001(4) 0.022(4) 0.056(5) C25 0.095(5) 0.077(5) 0.058(4) 0.001(3) 0.018(4) 0.053(4) C26 0.060(4) 0.062(4) 0.063(4) -0.007(3) 0.003(3) 0.012(4) C27 0.048(4) 0.065(4) 0.074(4) -0.007(3) 0.017(3) 0.024(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 S13 2.1999(14) . ? Ni1 S13 2.1999(14) 2_577 ? Ni1 S11 2.2089(12) . ? Ni1 S11 2.2089(12) 2_577 ? S11 C12 1.698(5) . ? C12 O14 1.306(5) . ? C12 S13 1.680(5) . ? O14 C15 1.482(5) . ? C15 C20 1.502(6) . ? C15 C16 1.512(5) . ? C15 H15 0.9800 . ? C16 C17 1.516(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N18 1.462(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? N18 C21 1.460(6) . ? N18 C19 1.460(5) . ? C19 C20 1.520(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.505(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C27 1.372(7) . ? C22 C23 1.371(6) . ? C23 C24 1.389(7) . ? C23 H23 0.9300 . ? C24 C25 1.352(7) . ? C24 H24 0.9300 . ? C25 C26 1.357(7) . ? C25 H25 0.9300 . ? C26 C27 1.387(7) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S13 Ni1 S13 180.00(9) . 2_577 ? S13 Ni1 S11 79.38(5) . . ? S13 Ni1 S11 100.62(5) 2_577 . ? S13 Ni1 S11 100.62(5) . 2_577 ? S13 Ni1 S11 79.38(5) 2_577 2_577 ? S11 Ni1 S11 179.999(1) . 2_577 ? C12 S11 Ni1 83.52(16) . . ? O14 C12 S13 120.7(4) . . ? O14 C12 S11 126.4(4) . . ? S13 C12 S11 112.9(3) . . ? C12 S13 Ni1 84.19(18) . . ? C12 O14 C15 120.0(4) . . ? O14 C15 C20 110.5(3) . . ? O14 C15 C16 105.9(4) . . ? C20 C15 C16 111.1(4) . . ? O14 C15 H15 109.8 . . ? C20 C15 H15 109.8 . . ? C16 C15 H15 109.8 . . ? C17 C16 C15 109.6(4) . . ? C17 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? C17 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? N18 C17 C16 110.3(4) . . ? N18 C17 H17A 109.6 . . ? C16 C17 H17A 109.6 . . ? N18 C17 H17B 109.6 . . ? C16 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? C21 N18 C19 110.3(4) . . ? C21 N18 C17 111.3(4) . . ? C19 N18 C17 108.9(4) . . ? N18 C19 C20 110.2(4) . . ? N18 C19 H19A 109.6 . . ? C20 C19 H19A 109.6 . . ? N18 C19 H19B 109.6 . . ? C20 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? C15 C20 C19 109.2(4) . . ? C15 C20 H20A 109.8 . . ? C19 C20 H20A 109.8 . . ? C15 C20 H20B 109.8 . . ? C19 C20 H20B 109.8 . . ? H20A C20 H20B 108.3 . . ? N18 C21 C22 113.9(4) . . ? N18 C21 H21A 108.8 . . ? C22 C21 H21A 108.8 . . ? N18 C21 H21B 108.8 . . ? C22 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C27 C22 C23 117.7(5) . . ? C27 C22 C21 121.8(5) . . ? C23 C22 C21 120.3(5) . . ? C22 C23 C24 120.2(6) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C25 C24 C23 121.2(5) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C24 C25 C26 119.5(6) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? C25 C26 C27 119.6(6) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C22 C27 C26 121.7(5) . . ? C22 C27 H27 119.1 . . ? C26 C27 H27 119.1 . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.344 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.083 data_4 _database_code_depnum_ccdc_archive 'CCDC 913786' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 N4 Ni S4' _chemical_formula_weight 605.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4456(14) _cell_length_b 10.110(2) _cell_length_c 11.407(3) _cell_angle_alpha 76.000(19) _cell_angle_beta 80.634(19) _cell_angle_gamma 73.41(2) _cell_volume 687.7(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5137 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 27.50 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 314 _exptl_absorpt_coefficient_mu 1.035 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.59515 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 5137 _diffrn_reflns_av_R_equivalents 0.0659 _diffrn_reflns_av_sigmaI/netI 0.1074 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3018 _reflns_number_gt 1792 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1171P)^2^+0.6119P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3018 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1379 _refine_ls_R_factor_gt 0.0867 _refine_ls_wR_factor_ref 0.2835 _refine_ls_wR_factor_gt 0.2541 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.132 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N14 N 0.3980(9) 0.1405(6) 0.1449(5) 0.0472(14) Uani 1 1 d . . . S11 S 0.1845(3) 0.1613(2) -0.04560(18) 0.0550(5) Uani 1 1 d . . . S13 S 0.1328(3) -0.0313(2) 0.17324(19) 0.0550(6) Uani 1 1 d . . . Ni1 Ni 0.0000 0.0000 0.0000 0.0486(5) Uani 1 2 d S . . C12 C 0.2632(11) 0.0983(7) 0.0983(7) 0.0459(16) Uani 1 1 d . . . C21 C 0.4702(12) 0.0698(8) 0.2655(8) 0.0574(19) Uani 1 1 d . . . H21A H 0.6262 0.0567 0.2607 0.069 Uiso 1 1 calc R . . H21B H 0.4430 -0.0230 0.2862 0.069 Uiso 1 1 calc R . . C22 C 0.3633(12) 0.1463(8) 0.3667(7) 0.0555(19) Uani 1 1 d . B . C23 C 0.4864(16) 0.1840(10) 0.4325(8) 0.072(2) Uani 1 1 d . . . H23 H 0.6362 0.1630 0.4122 0.086 Uiso 1 1 calc R A 1 N24 N 0.4039(19) 0.2498(12) 0.5251(8) 0.100(3) Uani 1 1 d . . . C25 C 0.189(2) 0.2796(13) 0.5513(10) 0.107(4) Uani 1 1 d . . . H25 H 0.1289 0.3237 0.6162 0.129 Uiso 1 1 calc R B 1 C26 C 0.0509(19) 0.2493(14) 0.4886(11) 0.112(4) Uani 1 1 d . B . H26 H -0.0990 0.2759 0.5075 0.135 Uiso 1 1 calc R . . C27 C 0.1413(14) 0.1786(11) 0.3973(9) 0.085(3) Uani 1 1 d . . . H27 H 0.0526 0.1521 0.3554 0.101 Uiso 1 1 calc R B . C31 C 0.5059(13) 0.2495(9) 0.0719(7) 0.060(2) Uani 1 1 d . . . H31A H 0.4374 0.2910 -0.0028 0.072 Uiso 1 1 calc R . . H31B H 0.6570 0.2042 0.0502 0.072 Uiso 1 1 calc R . . C32 C 0.4976(11) 0.3648(7) 0.1352(6) 0.0462(16) Uani 1 1 d . D . C33 C 0.2976(13) 0.4612(9) 0.1573(8) 0.068(2) Uani 1 1 d . . . H33 H 0.1718 0.4543 0.1319 0.081 Uiso 1 1 calc R C 1 C34 C 0.2894(17) 0.5651(9) 0.2161(10) 0.090(3) Uani 1 1 d . . . H34 H 0.1574 0.6292 0.2311 0.108 Uiso 1 1 calc R B 1 C35 C 0.472(2) 0.5754(10) 0.2529(10) 0.088(3) Uani 1 1 d . . . H35 H 0.4636 0.6462 0.2940 0.106 Uiso 1 1 calc R D 1 C36 C 0.6707(16) 0.4835(10) 0.2309(10) 0.084(3) Uani 1 1 d . . . H36 H 0.7963 0.4914 0.2557 0.101 Uiso 1 1 calc R B 1 C37 C 0.6768(12) 0.3810(9) 0.1719(8) 0.061(2) Uani 1 1 d . . . H37 H 0.8103 0.3188 0.1558 0.073 Uiso 1 1 calc R D 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N14 0.042(3) 0.058(3) 0.047(3) -0.021(3) 0.000(3) -0.013(3) S11 0.0570(11) 0.0641(12) 0.0519(11) -0.0154(9) -0.0048(9) -0.0257(9) S13 0.0598(12) 0.0567(11) 0.0573(12) -0.0136(9) -0.0092(9) -0.0251(9) Ni1 0.0438(7) 0.0547(8) 0.0549(9) -0.0213(6) -0.0048(6) -0.0161(6) C12 0.042(4) 0.049(4) 0.047(4) -0.022(3) 0.001(3) -0.003(3) C21 0.044(4) 0.063(5) 0.070(5) -0.022(4) -0.012(4) -0.012(3) C22 0.055(4) 0.059(4) 0.058(5) -0.015(4) -0.009(4) -0.020(3) C23 0.074(6) 0.095(7) 0.057(5) -0.027(5) -0.001(4) -0.033(5) C24 0.119(9) 0.147(9) 0.061(6) -0.048(6) -0.001(6) -0.058(7) N24 0.119(9) 0.147(9) 0.061(6) -0.048(6) -0.001(6) -0.058(7) C25 0.126(11) 0.146(11) 0.065(7) -0.062(7) 0.023(7) -0.041(8) C26 0.084(8) 0.173(12) 0.087(8) -0.074(8) 0.018(6) -0.018(8) C27 0.055(5) 0.132(9) 0.084(7) -0.057(6) 0.002(5) -0.027(5) C31 0.053(4) 0.085(6) 0.055(5) -0.028(4) 0.011(4) -0.036(4) C32 0.047(4) 0.058(4) 0.037(4) -0.011(3) 0.003(3) -0.021(3) C33 0.051(5) 0.075(6) 0.076(6) -0.014(5) -0.008(4) -0.016(4) C34 0.084(7) 0.065(6) 0.107(8) -0.025(5) 0.015(6) -0.003(5) N34 0.084(7) 0.065(6) 0.107(8) -0.025(5) 0.015(6) -0.003(5) C35 0.121(9) 0.063(6) 0.091(8) -0.034(5) 0.004(7) -0.031(6) C36 0.087(7) 0.079(6) 0.107(8) -0.035(6) -0.019(6) -0.036(5) N36 0.087(7) 0.079(6) 0.107(8) -0.035(6) -0.019(6) -0.036(5) C37 0.047(4) 0.072(5) 0.068(5) -0.019(4) -0.004(4) -0.022(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N14 C12 1.300(9) . ? N14 C21 1.471(9) . ? N14 C31 1.481(9) . ? S11 C12 1.714(7) . ? S11 Ni1 2.2004(19) . ? S13 C12 1.735(7) . ? S13 Ni1 2.198(2) . ? Ni1 S13 2.198(2) 2 ? Ni1 S11 2.2004(19) 2 ? C21 C22 1.508(11) . ? C22 C23 1.358(11) . ? C22 C27 1.379(11) . ? C23 N24 1.341(13) . ? C23 C24 1.341(13) . ? C24 C25 1.331(15) . ? N24 C25 1.331(15) . ? C25 C26 1.365(16) . ? C26 C27 1.364(14) . ? C31 C32 1.498(10) . ? C32 C37 1.355(9) . ? C32 C33 1.404(11) . ? C33 N34 1.361(13) . ? C33 C34 1.361(13) . ? C34 C35 1.352(14) . ? N34 C35 1.352(14) . ? C35 N36 1.376(14) . ? C35 C36 1.376(14) . ? C36 C37 1.354(12) . ? N36 C37 1.354(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N14 C21 121.3(6) . . ? C12 N14 C31 120.9(6) . . ? C21 N14 C31 117.4(6) . . ? C12 S11 Ni1 85.9(3) . . ? C12 S13 Ni1 85.5(2) . . ? S13 Ni1 S13 180.00(4) . 2 ? S13 Ni1 S11 79.35(7) . . ? S13 Ni1 S11 100.65(7) 2 . ? S13 Ni1 S11 100.65(7) . 2 ? S13 Ni1 S11 79.35(7) 2 2 ? S11 Ni1 S11 180.00(6) . 2 ? N14 C12 S11 125.9(6) . . ? N14 C12 S13 125.0(6) . . ? S11 C12 S13 109.0(4) . . ? N14 C21 C22 115.3(6) . . ? C23 C22 C27 117.6(8) . . ? C23 C22 C21 120.1(7) . . ? C27 C22 C21 122.3(7) . . ? N24 C23 C24 0.0(12) . . ? N24 C23 C22 123.6(9) . . ? C24 C23 C22 123.6(9) . . ? C25 C24 C23 116.8(9) . . ? C25 N24 C23 116.8(9) . . ? N24 C25 C24 0.0(11) . . ? N24 C25 C26 124.0(10) . . ? C24 C25 C26 124.0(10) . . ? C27 C26 C25 117.5(11) . . ? C26 C27 C22 120.4(9) . . ? N14 C31 C32 114.1(6) . . ? C37 C32 C33 118.1(8) . . ? C37 C32 C31 122.5(7) . . ? C33 C32 C31 119.4(7) . . ? N34 C33 C34 0.0(8) . . ? N34 C33 C32 119.4(8) . . ? C34 C33 C32 119.4(8) . . ? C35 C34 C33 120.3(9) . . ? C35 N34 C33 120.3(9) . . ? N34 C35 C34 0.0(11) . . ? N34 C35 N36 121.4(9) . . ? C34 C35 N36 121.4(9) . . ? N34 C35 C36 121.4(9) . . ? C34 C35 C36 121.4(9) . . ? N36 C35 C36 0.0(10) . . ? C37 C36 C35 117.7(9) . . ? C37 N36 C35 117.7(9) . . ? N36 C37 C36 0.0(7) . . ? N36 C37 C32 123.1(8) . . ? C36 C37 C32 123.1(8) . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.784 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.109